Orgo 1 Review I Need (Synthesis)

alkyne to alkene

H2, Lindler’s catalyst

OR

Na, NH3

alkene to alkyne

1) Br2

2) xs NaNH2

3) H2O

alkene to alkane

H2, Pd, Pt, or Ni

alkane to alkyl halide

Br2, hv

alkyl halide to alkene

NaOMe (more sub pos)

OR

t-BuOK (less sub pos)

alkene to alkyl halide

HX (mark, x at most sub)

HX, ROOR (antimark, x at less sub)

alkyl halide to alcohol

NaOH (SN2)

OR

H2O (SN1)

alcohol to alkyl halide

HX

OR

SOCl2, py

OR

PBr3

alcohol to alkene

conc. H2SO4, heat

OR
1) TSCL, py

2) NaOMe

alkene to alcohol

H3O (syn, OH on more sub)

OR

1) BH3*THF

2) H2O2, NaOH (anti, OH on les sub)

OR

1) Hg(OAc)2

2) NaBH4, NaOH (syn, OH on more sub)

alkyne to ketone/aldehyde

H2SO4, H2O, HgSO4 (carbonyl on more sub pos)

OR

1) R2BH

2) H2O2, NaOH (carbonyl on less sub pos)

ketone/aldehyde to alcohol

1) LiAlH4

2) H2O

OR

NaBH4, MeOH

alcohol to ketone/aldehyde

H2CrO4

OR

PCC

OR

DMP

OR

Swern